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Most frequently booked Cheshire hotels
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Hotel Downstreet
40 Main St, North Adams, MA
Free cancellation
Reserve now, pay when you stay
15.79 km from city centre
The price is CA $167 per night
CA $167
CA $187 total
includes taxes & fees
9 Mar - 10 Mar
Stay at this 3-star hotel in North Adams. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Massachusetts Museum of Contemporary Art and Studio 21 South are located nearby.
Pool
Hot tub
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Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free cancellation
Reserve now, pay when you stay
10.45 km from city centre
The price is CA $139 per night
CA $139
CA $167 total
includes taxes & fees
2 Mar - 3 Mar
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and in-room massages. Our guests praise the helpful staff in our reviews. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located nearby.
Pool
Kitchen
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Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
21.55 km from city centre
The price is CA $151 per night
CA $151
CA $169 total
includes taxes & fees
7 Mar - 8 Mar
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel
190 Meadow Street, South Lee, MA
Free cancellation
33.29 km from city centre
The price is CA $169 per night
CA $169
CA $208 total
includes taxes & fees
2 Mar - 3 Mar
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Restaurant
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The Williams Inn
101 Spring Street, Williamstown, MA
Free cancellation
Reserve now, pay when you stay
16.77 km from city centre
The price is CA $254 per night
CA $254
CA $284 total
includes taxes & fees
23 Feb - 24 Feb
Stay at this 4-star business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Williams College Museum of Art and Chapin Library of Rare Books and Manuscripts are located nearby.
Pet-friendly
Parking included
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The Red Lion Inn
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
33.43 km from city centre
The price is CA $211 per night
CA $211
CA $299 total
includes taxes & fees
2 Mar - 3 Mar
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Schantz Galleries and Mission House are located nearby.
Pool
Spa
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The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
19.61 km from city centre
The price is CA $113 per night
CA $113
CA $127 total
includes taxes & fees
2 Mar - 3 Mar
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Guido's Marketplace and Bousquet Ski Area are located nearby.
Pool
Hot tub
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Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
One West Street, Pittsfield, MA
Free cancellation
14.75 km from city centre
The price is CA $147 per night
CA $147
CA $165 total
includes taxes & fees
7 Mar - 8 Mar
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Berkshire Museum and Colonial Theater are located nearby.
Pool
Pet-friendly

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Free cancellation
18.58 km from city centre
The price is CA $183 per night
CA $183
CA $233 total
includes taxes & fees
2 Mar - 3 Mar
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Guido's Marketplace and Arrowhead Museum are located nearby.
Pool
Hot tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top hotels in Cheshire for Extended Stay
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The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
10/10 Exceptional! (2 reviews)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Cheshire hotels essential information
Accommodation | 950 hotels |
---|---|
Lowest Price | CA $113 |
Highest Price | CA $254 |
Popular hotels | Hotel Downstreet, Vacation Village in the Berkshires, Life House Berkshires, Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires, an IHG Hotel, The Williams Inn, The Red Lion Inn, The Yankee, Trademark Collection by Wyndham, Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel, Berkshire Mountain Lodge |
Frequently asked questions
Recent Cheshire hotel reviews by fellow wanderers
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Life House Berkshires
5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Nice room, the lobby, bar, and food lounge area also very nice. Food was good with limited choices, which worked for me."
A verified traveller stayed at Life House Berkshires
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